Tetrabutylammonium Fluoride → HCID 10088309, compound

HRID 654312Notes

Reaction equation

HRID 654312 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@@H:10]([O:17][Si](C(C)(C)C)(C)C)/[CH:11]=[CH:12]/[C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C@@H:10]([OH:17])/[CH:11]=[CH:12]/[C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10742163HCID 10742163, compound

Product 1

HCID 10088309HCID 10088309, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.0 g (2.2 mmol) of the resultant compound of Example 18 in 8 ml of tetrahydrofuran was treated with 2.2 ml (2.2 mmol) of a 1.0M solution of tetra-n-butylammonium fluoride in tetrahydrofuran. After being stirred under N2 atmosphere at ambient temperature for 2 h, the solution was concentrated in vacuo, and the residue was partitioned between ethyl acetate and brine. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. Chromatography of the residue on silica gel using 4:1 hexane:ethyl acetate provided 0.36 g (47%) of the desired compound.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and brine
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e21bce0cb1d4b6c801241e411451347
Source dataset
uspto-grants-1992_07
Patent number
US05130468

Reaction notes

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